The Rocks & Chains Tour

Sydney’s Origin Story — Grit, Grog & Chains

Sydney’s Origin Story — Grit, Grog & Chains

January 1788: over 1,400 convicts, marines, and officials spilled off the First Fleet into Sydney Cove. The Eora people had been here for tens of thousands of years — and let’s just say they didn’t exactly roll out the welcome mat. What followed wasn’t polite colonisation, but the

Empire’s wildest outpost: a jail, a port, and a city built on chains, rum, and rebellion. For nearly 80 years, Sydney was the British Empire’s rowdiest frontier — a place of culture clashes, backbreaking labour, and more scandal than order. And out of all that grit came the rough humour and survival instinct that still defines the city today.

What You’ll Dig Up

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1.Clash of worlds

Eora Country meets convicts, marines, and misfits.

2.Convicts vs captains

Crime, punishment, and the defiance that kept things interesting.

3.Larrikins & legends

Crime, punishment, and the defiance that kept things interesting.

4.Hidden history

Alleys and corners where the plaques stay quiet.

Tour Details

Meeting Point

Alleys and corners where the plaques stay quiet.

Group size (Max 15)

Small enough for secrets, rowdy enough for laughs.

Best for

Anyone who loves a story with bite — from first-timers to locals who think they

know Sydney.

Your guide (Ed)

Passionate storyteller, history tragic, cheeky local.

Duration (2 hours)

Vivid stories and sandstone secrets (wear comfy shoes).

Meeting Point

Alleys and corners where the plaques stay quiet.

Group size (Max 15)

Small enough for secrets, rowdy enough for laughs.

Best for

Anyone who loves a story with bite — from first-timers to locals who think they

know Sydney.

Your guide (Ed)

Passionate storyteller, history tragic, cheeky local.

Duration (2 hours)

Vivid stories and sandstone secrets (wear comfy shoes).

1

The real origin story of Sydney, raw and unpolished.

2

A deeper sense of the larrikin streak that still runs through Sydney today.

3

A gritty new lens on the city’s foundations.

Don’t Just Visit Sydney. Roam Its History.

Small groups. Big stories. Tours that sell out fast — slip the leash and join the pack.